Substituted thien-3-yl-sulphonylamino(thio)carbonyl-triazolin(ethi)ones

ABSTRACT

The invention relates to novel substituted thien-3-yl-sulphonylamino(thio)carbonyl-triazolin(ethi)ones of the general formula (I)  
                 
in which 
         Q 1 , Q 2 , R 1 , R 2 , R 3  and R 4  are each as defined in the description, and to salts of the compounds according to formula (I), to processes and to novel intermediates for their preparation and to their use as herbicides.

The invention relates to novel substitutedthien-3-yl-sulphonylamino(thio)carbonyl-triazolin(ethi)ones, toprocesses and novel intermediates for their preparation and to their useas herbicides.

It is already known that certain substitutedthienylsulphonylamino(thio)carbonyl-triazolin(ethi)ones have herbicidalproperties (cf. WO-A-97/16449, WO-A-98/24787). However, the activity ofthese compounds is not entirely satisfactory.

This invention, accordingly, provides the novel substitutedthien-3-yl-sulphonylamino(thio)carbonyl-triazolin(ethi)ones of thegeneral formula (I)

in which

-   -   Q¹ represents O (oxygen) or S (sulphur),    -   Q² represents O (oxygen) or S (sulphur),    -   R¹ represents in each case optionally substituted alkyl,        alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl,        heterocyclyl- or heterocyclylalkyl,    -   R² represents hydrogen, cyano, nitro, halogen or represents in        each case optionally substituted alkyl, alkoxy, alkoxycarbonyl,        alkylthio, alkylsulphinyl, alkylsulphonyl, alkenyl, alkinyl,        alkenyloxy or alkinyloxy,    -   R³ represents hydrogen, hydroxyl, mercapto, amino, cyano,        halogen or represents in each case optionally substituted alkyl,        alkenyl, alkinyl, alkoxy, alkylthio, alkylamino,        alkylcarbonylamino, alkenyloxy, alkinyloxy, alkenylthio,        alkinylthio, alkenylamino, alkinylamino, dialkylamino,        aziridino, pyrrolidino, piperidino, morpholino, cycloalkyl,        cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino,        cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio,        cycloalkylalkylamino, aryl, arylalkyl, aryloxy, arylalkoxy,        arylthio, arylalkylthio, arylamino or arylalkylamino, and    -   R⁴ represents hydrogen, hydroxyl, amino, cyano, represents        alkylideneamino or represents in each case optionally        substituted alkyl, alkenyl, alkinyl, alkoxy, alkylamino,        alkyl-carbonylamino, alkenyloxy, dialkylamino, cycloalkyl,        cycloalkylamino, cycloalkylalkyl, aryl or arylalkyl, or    -   R³ and R⁴ together represent optionally branched alkanediyl,    -   and salts of the compounds of the formula (I)—.

Saturated or unsaturated hydrocarbon groupings, such as alkyl,alkanediyl, alkenyl or alkinyl, are in each case straight-chain orbranched as far as this is possible—including in combination withheteroatoms, such as in alkoxy.

Optionally substituted radicals can be mono- or polysubstituted, where,in the case of polysubstitution, the substituents can be identical ordifferent.

Preferred substituents or ranges of the radicals present in the formulaegiven above and below are defined below.

Q¹ preferably represents O (oxygen) or S (sulphur).

Q² preferably represents O (oxygen) or S (sulphur).

R¹ preferably represents optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents ineach case optionally cyano- or halogen-substituted alkenyl or alkinylhaving in each case 2 to 6 carbon atoms, represents in each caseoptionally cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl orcycloalkylalkyl having in each case 3 to 6 carbon atoms in thecycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety,represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted aryl or arylalkyl having ineach case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4carbon atoms in the alkyl moiety, or represents in each case optionallynitro-, cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substitutedheterocyclyl or heterocyclylalkyl having in each case up to 6 carbonatoms and additionally 1 to 4 nitrogen atoms and/or 1 to 2 oxygen orsulphur atoms in the heterocyclyl group and optionally 1 to 4 carbonatoms in the alkyl moiety.

R² preferably represents hydrogen, cyano, nitro, halogen, represents ineach case optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl,alkoxy, alkoxy-carbonyl, alkylthio, alkylsulphinyl or alkylsulphonylhaving in each case 1 to 6 carbon atoms in the alkyl group, orrepresents in each case optionally cyano- or halogen-substitutedalkenyl, alkinyl, alkenyloxy or alkinyloxy having in each case 2 to 6carbon atoms in the alkenyl or alkinyl group.

R³ preferably represents hydrogen, hydroxyl, mercapto, amino, cyano,fluorine, chlorine, bromine, iodine, represents optionally fluorine-,chlorine-, bromine-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- orC₁-C₄-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms,represents in each case optionally fluorine-, chlorine- and/orbromine-substituted alkenyl or alkinyl having in each case 2 to 6 carbonatoms, represents in each case optionally fluorine-, chlorine-, cyano-,C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substituted alkoxy, alkylthio,alkylamino or alkylcarbonylamino having in each case 1 to 6 carbon atomsin the alkyl group, represents alkenyloxy, alkinyloxy, alkenylthio,alkinylthio, alkenylamino or alkinylamino having in each case 3 to 6carbon atoms in the alkenyl or alkinyl group, represents dialkylaminohaving in each case 1 to 4 carbon atoms in the alkyl groups, representsin each case optionally methyl- and/or ethyl-substituted aziridino,pyrrolidino, piperidino or morpholino, represents in each caseoptionally fluorine-, chlorine-, bromine-, cyano- and/orC₁-C₄-alkyl-substituted cycloalkyl, cycloalkenyl, cycloalkyloxy,cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy,cycloalkylalkylthio or cycloalkylalkylamino having in each case 3 to 6carbon atoms in the cycloalkyl or cycloalkenyl group and optionally 1 to4 carbon atoms in the alkyl moiety, or represents in each caseoptionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C₁-C₄-alkyl-,trifluoromethyl-, C₁-C₄-alkoxy- and/or C₁-C₄-alkoxy-carbonyl-substitutedaryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylaminoor arylalkylamino having in each case 6 or 10 carbon atoms in the arylgroup and optionally 1 to 4 carbon atoms in the alkyl moiety.

R⁴ preferably represents hydrogen, hydroxyl, amino, cyano, representsC₂-C₁₀-alkylideneamino, represents optionally fluorine-, chlorine-,bromine-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- orC₁-C₄-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms,represents in each case optionally fluorine-, chlorine- and/orbromine-substituted alkenyl or alkinyl having in each case 2 to 6 carbonatoms, represents in each case optionally fluorine-, chlorine-,bromine-, cyano-, C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substitutedalkoxy, alkylamino or alkylcarbonylamino having in each case 1 to 6carbon atoms in the alkyl group, represents alkenyloxy having 3 to 6carbon atoms, represents dialkylamino having in each case 1 to 4 carbonatoms in the alkyl groups, represents in each case optionally fluorine-,chlorine-, bromine-, cyano- and/or C₁-C₄-alkyl-substituted cycloalkyl,cycloalkylamino or cycloalkylalkyl having in each case 3 to 6 carbonatoms in the alkyl group and optionally 1 to 4 carbon atoms in the alkylmoiety, or represents in each case optionally fluorine-, chlorine-,bromine-, cyano-, nitro-, C₁-C₄-alkyl-, trifluoromethyl- and/orC₁-C₄-alkoxy-substituted aryl or arylalkyl having in each case 6 or 10carbon atoms in the aryl group and optionally l to 4 carbon atoms in thealkyl moiety.

R³ and R⁴ together also preferably represent optionally branchedalkanediyl having 3 to 6 carbon atoms.

Q¹ particularly preferably represents O (oxygen) or S (sulphur).

Q² particularly preferably represents O (oxygen) or S (sulphur).

R¹ particularly preferably represents in each case optionally cyano-,fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, represents in each case optionallycyano-, fluorine- or chlorine-substituted propenyl, butenyl, propinyl orbutinyl, represents in each case optionally cyano-, fluorine-,chlorine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl or cyclohexylmethyl, represents in each caseoptionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenylmethyl orphenylethyl, or represents in each case optionally cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, methoxy-,ethoxy-, n- or i-propoxy-substituted heterocyclyl or heterocyclylmethyl,where the heterocyclyl group is in each case selected from the groupconsisting of oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl,tetrahydrothienyl.

R² particularly preferably represents hydrogen, cyano, fluorine,chlorine, bromine, represents in each case optionally cyano-, fluorine-,chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio,ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl,methylsulphonyl or ethylsulphonyl, or represents in each case optionallycyano-, fluorine- or chlorine-substituted propenyl, butenyl, propinyl,butinyl, propenyloxy, butenyloxy, propinyloxy or butinyloxy.

R³ particularly preferably represents hydrogen, hydroxyl, mercapto,amino, cyano, fluorine, chlorine, bromine, represents in each caseoptionally fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- ori-propoxy, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-,ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, represents in each case optionallyfluorine-, chlorine- and/or bromine-substituted ethenyl, propenyl,butenyl, ethinyl, propinyl or butinyl, represents in each caseoptionally fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- ori-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-,s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- ort-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- ort-butylamino, acetylamino or propionylamino, represents propenyloxy,butenyloxy, ethinyloxy, propinyloxy, butinyloxy, propenylthio,butenylthio, propinylthio, butinylthio, propenylamino, butenylamino,propinylamino or butinylamino, represents dimethylamino, diethylamino ordipropylamino, represents in each case optionally fluorine-, chlorine-,methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy,cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio,cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino,cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy,cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy,cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio,cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino,cyclopentylmethylamino or cyclohexylmethylamino, or represents in eachcase optionally fluorine-, chlorine-, bromine-, methyl-,trifluoromethyl-, methoxy- or methoxy-carbonyl-substituted phenyl,benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino orbenzylamino.

R⁴ particularly preferably represents hydrogen, hydroxyl, amino,represents in each case optionally fluorine-, chlorine-, cyano-,methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, represents in each case optionally fluorine-, chlorine-and/or bromine-substituted ethenyl, propenyl, butenyl, propinyl orbutinyl, represents in each case optionally fluorine-, chlorine-,cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy,n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino,n-, i-, s- or t-butylamino, represents propenyloxy or butenyloxy,represents dimethylamino or diethylamino, represents in each caseoptionally fluorine-, chlorine-, methyl- and/or ethyl-substitutedcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino,cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or representsin each case optionally fluorine-, chlorine-, methyl-, trifluoromethyl-and/or methoxy-substituted phenyl or benzyl.

R³ and R⁴ together also particularly preferably represent trimethylene(propan-1,3-diyl), tetramethylene (butan-1,4-diyl) or pentamethylene(pentane-1,5-diyl).

Q¹ very particularly preferably represents O (oxygen).

Q² very particularly preferably represents O (oxygen).

R¹ very particularly preferably represents in each case optionallyfluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n-or i-propyl.

R² very particularly preferably represents fluorine, chlorine, bromineor represents in each case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl.

R³ very particularly preferably represents hydrogen, chlorine, bromine,represents in each case optionally fluorine-, chlorine-, methoxy-,ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl,represents in each case optionally fluorine- or chlorine-substitutedethenyl, propenyl, butenyl, propinyl or butinyl, represents in each caseoptionally fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio,ethylthio, n- or i-propylthio, methylamino, ethylamino, n- ori-propylamino, represents propenyloxy, propinyloxy, propenylthio,propinylthio, propenylamino or propinylamino, represents dimethylaminoor diethylamino, represents in each case optionally fluorine-, chlorine-or methyl-substituted cyclopropyl, cyclopropyloxy, cyclopropylmethyl orcyclopropylmethoxy.

R⁴ very particularly preferably represents in each case optionallyfluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n-or i-propyl, represents in each case optionally fluorine- orchlorine-substituted ethenyl, propenyl or propinyl, represents in eachcase optionally fluorine-, chlorine-, methoxy- or ethoxy-substitutedmethoxy, ethoxy, n- or i-propoxy, represents methylamino, or representscyclopropyl.

R¹ most preferably represents methyl, ethyl, n- or i-propyl.

R² most preferably represents methyl, ethyl, n- or 1-propyl.

R³ most preferably represents methoxy, ethoxy, n- or i-propoxy, methyl,ethyl, n- or i-propyl, methylthio, ethylthio, n- or i-propylthio orcyclopropyl.

R⁴ most preferably represents methyl, ethyl, n- or i-propyl orcyclopropyl.

The invention also preferably provides the sodium, potassium, magnesium,calcium, ammonium, C₁-C₄-alkyl-ammonium-, di-(C₁-C₄-alkyl)-ammonium,tri-(C₁-C₄-alkyl)-ammonium, tetra-(C₁-C₄-alkyl)-ammonium,tri-(C₁-C₄-alkyl)-sulphonium, C₅- or C₆-cycloalkyl-ammonium anddi-(C₁-C₂-alkyl)-benzyl-ammonium salts of compounds of the formula (I)in which Q¹, Q², R¹, R², R³ and R⁴ each preferably have the meaningsgiven above.

The abovementioned general or preferred radical definitions apply bothto the end products of the formula (I) and, correspondingly, to thestarting materials or intermediates required in each case for thepreparation. These radical definitions can be combined with one anotheras desired, i.e. including combinations between the given preferredranges.

Preference according to the invention is given to those compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred.

Particular preference according to the invention is given to thosecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to thosecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

The novel substitutedthien-3-yl-sulphonylamino(thio)carbonyl-triazolin(ethi)ones of thegeneral formula (I) have interesting biological properties. Inparticular,.they have strong herbicidal activity.

The novel substitutedthien-3-yl-sulphonylamino(thio)carbonyl-triazolin(ethi)ones of thegeneral formula (I) are obtained when

-   -   (a) substituted thiophene-3-sulphonamides of the general formula        (II)        in which    -   R¹ and R² are each as defined above,    -   are reacted with substituted triazolin(ethi)ones of the general        formula (III)        in which    -   Q¹, Q², R³ and R⁴ are each as defined above and    -   Z represents halogen, alkoxy, aryloxy or arylalkoxy,    -   if appropriate in the presence of a reaction auxiliary and if        appropriate in the presence of a diluent,        or when    -   (b) substituted thien-3-yl-sulphonyl iso(thio)cyanates of the        general formula (IV)        in which    -   Q¹, R¹ and R² are each as defined above,    -   are reacted with triazolin(ethi)ones of the general formula (V)        in which    -   Q², R⁴ and R⁵ are each as defined above,    -   if appropriate in the presence of a reaction auxiliary and if        appropriate in the presence of a diluent,        or when    -   (c) substituted thiophene-3-sulphonyl chlorides of the general        formula (VI)        in which    -   R¹ and R² are each as defined above,    -   are reacted with triazolin(ethi)ones of the general formula (V)        in which    -   Q², R⁴ and R⁵ are each as defined above,    -   and metal (thio)cyanates of the general formula (VII)        M-Q¹-CN   (VII)        in which    -   Q¹ is as defined above,    -   if appropriate in the presence of a reaction auxiliary and if        appropriate in the presence of a diluent,        or when    -   (d) substituted thiophene-3-sulphonyl chlorides of the general        formula (VI)        in which    -   R¹ and R² are each as defined above,    -   are reacted with triazolin(ethi)one-(thio)carboxamides of the        general formula (VIII)        in which    -   Q¹, Q², R³ and R⁴ are each as defined above,    -   if appropriate in the presence of a reaction auxiliary and if        appropriate in the presence of a diluent,        or when    -   (e) substituted thien-3-yl-sulphonylamino(thio)carbonyl        compounds of the general formula (IX)        in which    -   Q¹, R¹ and R² are each as defined above and    -   Z represents halogen, alkoxy, aryloxy or arylalkoxy,    -   are reacted with triazolin(ethi)ones of the general formula (V)        in which    -   Q², R⁴ and R⁵ are each as defined above,    -   if appropriate in the presence of a reaction auxiliary and if        appropriate in the presence of a diluent,    -   and the compounds of the formula (I) obtained by the processes        (a), (b), (c), (d) or (e) are, if appropriate, converted by        customary methods into salts.

Using, for example, 2-chloro-4-ethoxycarbonyl-thiophene-3-sulphonamideand 4,5-dimethoxy-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-oneas starting materials, the course of the reaction in the process (a)according to the invention can be illustrated by the following formulascheme:

Using, for example, 2-fluoro-4-methoxycarbonyl-thien-3-yl-sulphonylisothiocyanate and 5-ethoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-oneas starting materials, the course of the reaction in the process (b)according to the invention can be illustrated by the following formulascheme:

Using, for example,4-methoxycarbonyl-2-trifluoromethyl-thiophene-3-sulphonyl chloride,5-ethyl-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-thione and potassiumcyanate as starting materials, the course of the reaction in the process(c) according to the invention can be illustrated by the followingformula scheme:

Using, for example, 3-ethoxycarbonyl-2-methyl-thiophene-4-sulphonylchloride and4-ethyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one-2-carboxamide asstarting materials, the course of the reaction in the process (d)according to the invention can be illustrated by the following formulascheme:

Using, for example, O-methylN-(2-ethyl-4-i-propoxycarbonyl-thien-3-yl-sulphonyl)-urethane and4,5-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials,the course of the reaction in the process (e) according to the inventioncan be illustrated by the following formula scheme:

The formula (II) provides a general definition of the substitutedthiophene-3-sulphonamides to be used as starting materials in theprocess (a) according to the invention for preparing compounds of thegeneral formula (I). In the general formula (II), R¹ and R² eachpreferably have those meanings which have already been mentioned above,in connection with the description of the compounds of the generalformula (I) according to the invention, as being preferred, or thosewhich have been mentioned in one of the particularly preferreddefinitions for R¹ and R².

Except for 4-methoxycarbonyl-thiophene-3-sulphonamide (cf. J. Org. Chem.45 (1980), 617-620), the substituted thiophene-3-sulphonamides of thegeneral formula (II) have hitherto not been disclosed in the literature;except for 4-methoxycarbonyl-thiophene-3-sulphonamide, they also form,as novel substances, part of the subject-matter of the presentapplication.

The substituted thiophene-3-sulphonamides of the general formula (II)are obtained when substituted thiophene-3-sulphonyl chlorides of thegeneral formula (VI)

in which

-   -   R¹ and R² are each as defined above,    -   are reacted with ammonium or ammonium salts, such as, for        example, ammonium acetate or ammonium carbonate, if appropriate        in the presence of a diluent, such as, for example, water or        methylene chloride, at temperatures between 0° C. and 100° C.        (cf. the. Preparation Examples).

The formula (III) provides a general definition of the substitutedtriazolin(ethi)ones furthermore to be used as starting materials in theprocess (a) according to the invention for preparing compounds of thegeneral formula (I). In the general formula (III), Q¹, Q², R³ and R⁴each preferably have those meanings which have already been mentionedabove, in connection with the description of the compounds of thegeneral formula (I) according to the invention, as being preferred, orthose which have been mentioned in one of the particularly preferreddefinitions for Q¹, Q², R³ and R⁴.

The starting materials of the general formula (III) are known and/or canbe prepared by processes known per se (cf. EP-A-341 489, EP-A-422 469,EP-A-425 948, EP-A-431 291, EP-A-507 171, EP-A-534 266).

The formula (IV) provides a general definition of the substitutedthien-3-yl-sulphonyl iso(thio)cyanates to be used as starting materialsin the process (b) according to the invention for preparing compounds ofthe general formula (I). In the general formula (IV), Q¹, R¹ and R² eachpreferably have those meanings which have already been mentioned above,in connection with the description of the compounds of the generalformula (I) according to the invention, as being preferred, or thosewhich have been mentioned in one of the particularly preferreddefinitions for Q¹, R¹ and R².

The starting materials of the general formula (IV) are known and/or canbe prepared by processes known per se (cf. U.S. Pat. No. 4,701,535).

The formula (V) provides a general definition of the triazolin(ethi)onesto be used as starting materials in the processes (b), (c) and (e)according to the invention for preparing compounds of the generalformula (I). In the general formula (V), Q², R⁴ and R⁵ each preferablyhave those meanings which have already been mentioned above, inconnection with the description of the compounds of the general formula(I) according to the invention, as being preferred, or those which havebeen mentioned in one of the particularly preferred definitions of Q²,R⁴ and R⁵.

The starting materials of the general formula (V) are known and/or canbe prepared by processes known per se (cf. EP-A-341 489, EP-A-422 469,EP-A-425 948, EP-A-431 291, EP-A-507 171, EP-A-534 266).

The formula (VI) provides a general definition of the substitutedthiophene-3-sulphonyl chlorides to be used as starting materials in theprocesses (c) and (d) according to the invention for preparing compoundsof the general formula (I). In the general formula (VI), R¹ and R² eachpreferably have those meanings which have already been mentioned above,in connection with the description of the compounds of the generalformula (I) according to the invention, as being preferred, or thosewhich have been mentioned in one of the particularly preferreddefinitions of R¹ and R².

Except for 4-methoxycarbonyl-thiophene-3-sulphonyl chloride (cf. J. Org.Chem. 45 (1980), 617-620), the substituted thiophene-3-sulphonylchlorides of the general formula (VI) have hitherto not been disclosedin the literature; except for 4-methoxy-carbonyl-thiophen-3-sulphonylchloride, they also form, as novel substances, part of thesubject-matter of the present application.

The substituted thiophene-3-sulphonyl chlorides of the general formula(VI) are obtained when 3-amino-thiophene-4-carboxylic esters of thegeneral formula (X)

in which

-   -   R¹ and R² are each as defined above,    -   or acid adducts of compounds of the formula (X), such as, for        example, the hydrochlorides    -   are reacted with an alkali metal nitrite, such as, for example,        sodium nitrite, in the presence of hydrochloric acid at        temperatures between −10° C. and +10° C., and the resulting        diazonium salt solution is reacted with sulphur dioxide in the        presence of a diluent, such as, for example, dichloromethane,        1,2-dichloro-ethane or acetic acid, and in the presence of a        catalyst, such as, for example, copper(I) chloride and/or        copper(II) chloride, at temperatures between −10° C. and +50° C.

The intermediates of the general formula (X) are known and/or can beprepared by processes known per se (cf. Austr. J. Chem. 48 (1995),1907-1916; Preparation Examples).

The formula (VIII) provides a general definition of thetriazolin(ethi)one-(thio)-carboxamides to be used as starting materialsin the process (d) according to the invention for preparing compounds ofthe general formula (I). In the general formula (VIII), Q¹, Q², R³ andR⁴ each preferably have those meanings which have already been mentionedabove, in connection with the description of the compounds of thegeneral formula (I) according to the invention, as being preferred, orthose which have been mentioned in one of the particularly preferreddefinitions for Q¹, Q², R³ and R⁴.

The starting materials of the general formula (VIII) are known and/orcan be prepared by processes known per se.

The formula (IX) provides a general definition of the substitutedthien-3-yl-sulphonylamino(thio)carbonyl compounds to be used as startingmaterials in the process (e) according to the invention for preparingcompounds of the general formula (I). In the general formula (IX), Q¹,R¹ and R² each preferably have those meanings which have already beenmentioned above, in connection with the description of the compounds ofthe general formula (I) according to the invention, as being preferred,or those which have been mentioned in one of the particularly preferreddefinitions for Q¹, R¹ and R².

The starting materials of the general formula (IX) are known and/or canbe prepared by processes known per se.

The processes (a), (b), (c), (d) and (e) according to the invention forpreparing the novel compounds of the formula (I) are preferably carriedout using diluents. Suitable diluents are virtually all inert organicsolvents. These preferably include aliphatic and aromatic, optionallyhalogenated hydrocarbons, such as pentane, hexane, heptane, cyclohexane,petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylenechloride, ethylene chloride, chloroform, carbon tetrachloride,chlorobenzene and o-dichlorobenzene, ethers such as diethyl ether anddibutyl ether, glycol dimethyl ether and diglycol dimethyl ether,tetrahydrofuran and dioxane, ketones, such as acetone, methyl ethylketone, methyl isopropyl ketone and methyl isobutyl ketone, esters, suchas methyl acetate and ethyl acetate, nitriles, such as, for example,acetonitrile and propionitrile, amides, such as, for example,dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and alsodimethyl sulphoxide, tetramethylene sulphone and hexamethyl phosphorictriamide.

Reaction auxiliaries suitable for the processes (a), (b), (c), (d) and(e) according to the invention are all acid binders which arecustomarily used for such reactions. Preference is given to alkali metalhydroxides, such as, for example, sodium hydroxide and potassiumhydroxide, alkaline earth metal hydroxides, such as, for example,calcium hydroxide, alkali metal carbonates and alkoxides, such as sodiumcarbonate and potassium carbonate, sodium tert-butoxide and potassiumtert-butoxide, furthermore basic nitrogen compounds, such astrimethylamine, triethylamine, tripropylamine, tributylamine,diisobutylamine, dicyclohexylamine, ethyldiisopropylamine,ethyldicyclohexylamine, N,N-dimethylbenzylamine, N,N-dimethyl-aniline,pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-,2-ethyl-, 4-ethyl- and 5-ethyl-2-methyl-pyridine,1,5-diazabicyclo[4.3.0]-non-5-ene (DBN),1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) and1,4-diazabicyclo[2.2.2]-octane (DABCO).

The reaction temperatures in the processes (a), (b), (c), (d) and (e)according to the invention can be varied within a relatively wide range.In general, the processes are carried out at temperatures between −20°C. and +150° C., preferably at temperatures between 0° C. and +100° C.

The processes (a), (b), (c), (d) and (e) according to the invention aregenerally carried out under atmospheric pressure. However, it is alsopossible to operate under elevated or reduced pressure.

For carrying out the processes (a), (b), (c), (d) and (e) according tothe invention, the starting materials required in each case aregenerally employed in approximately equimolar amounts. However, it isalso possible to use a relatively large excess of one of the componentsused in each case. The reactions are generally carried out in a suitablediluent in the presence of an acid acceptor, and the reaction mixture isstirred for several hours at the temperature required in each case.Work-up in the processes (a), (b), (c), (d) and (e) according to theinvention is in each case carried out by customary methods (cf. thePreparation Examples).

If appropriate, salts can be prepared from the compounds of the generalformula (I) according to the invention. Such salts are obtained in asimple manner by customary methods for forming salts, for example bydissolving or dispersing a compound of the formula (I) in a suitablesolvent, such as, for example, methylene chloride, acetone, tert-butylmethyl ether or toluene, and adding a suitable base. The salts canthen—if appropriate after prolonged stirring—be isolated byconcentration or filtration with suction.

The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weedkillers.By weeds in the broadest sense, there are to be understood all plantswhich grow in locations where they are not wanted. Whether thesubstances according to the invention act as total or selectiveherbicides depends essentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.

Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

According to the invention, it is possible to treat all plants and partsof plants. By plants are understood here all plants and plantpopulations such as desired and undesired wild plants or crop plants(including naturally occurring crop plants). Crop plants can be plantswhich can be obtained by conventional breeding and optimization methodsor by biotechnological and genetic engineering methods or combinationsof these methods, including transgenic plants and including plantvarieties which may or may not be protectable by plant variety propertyrights. Parts of plants are to be understood as meaning all above-groundand below-ground parts and organs of plants, such as shoot, leaf, flowerand root, examples which may be mentioned being leaves, needles, stems,trunks, flowers, shoot-bodies, fruits and seeds and also roots, andvegetative and generative propagation material, for example seedlings,tubers, rhizomes, cuttings and seeds.

The treatment of the plants and parts of plants according to theinvention with the active compounds is carried out directly or by actionon their environment, habitat or storage area according to customarytreatment methods, for example by dipping, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterials, in particular in the case of seeds, furthermore by single- ormulti-layer coating.

Depending on the concentration, the active compounds according to theinvention are suitable for total weed control, for example on industrialsites and rail tracks and on paths and areas with or without treegrowth. Equally, the compounds can be employed for controlling weeds inperennial crops, for example forests, ornamental tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hop fields, onlawns and turf and pastures and for selective weed control in annualcrops.

The compounds of the formula (I) according to the invention have strongherbicidal activity and a broad activity spectrum when applied on thesoil and on above-ground parts of plants. To a certain extent, they arealso suitable for selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous and dicotyledonous crops, bothby the pre-emergence and by the post-emergence method.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspo-emulsion concentrates,natural and synthetic substances impregnated with active compound, andmicroencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is to say liquid solventsand/or solid carriers, optionally with the use of surfactants, that isto say emulsifiers and/or dispersants and/or foam formers.

If the extender used is water, it is also possible to use, for example,organic solvents as auxiliary solvents. Liquid solvents which are mainlysuitable are: aromatics, such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons, such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons, such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols, such as butanol orglycol, and also their ethers and esters, ketones, such as acetone,methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, stronglypolar solvents, such as dimethylformamide and dimethyl sulphoxide, andwater.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks, such as calcite, marble, pumice, sepiolite, dolomite andsynthetic granules of inorganic and organic meals, and granules oforganic material, such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam formers are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand protein hydrolysates; suitable dispersants are: for examplelignosulphite waste liquors and methylcellulose.

Tackifiers, such as carboxymethylcellulose, natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, and also naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use dyestuffs, such as inorganic pigments, for exampleiron oxide, titanium oxide, Prussian blue, and organic dyestuffs, suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients, such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention,as such or in the form of their formulations, can also be used asmixtures with known herbicides, finished formulations or tank mixesbeing possible.

Possible components for the mixtures are known herbicides, for exampleacetochlor, acifluorfen(-sodium), aclonifen, alachlor,alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, anilofos,asulam, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl),benfuresate, bensulfuron(-methyl), bentazone, benzobicyclon, benzofenap,benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium),bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim, butylate,cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl),chlomethoxyfen, chloramben, chloridazon, chlorimuron(-ethyl),chlornitrofen, chlorsulfuron, chlorotoluron, cinidon(-ethyl),cinmethylin, cinosulfuron, clefoxydim, clethodim,clodinafop(-propargyl), clomazone, clomeprop, clopyralid,clopyrasulfuron(-methyl), cloransulam(-methyl), cumyluron, cyanazine,cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop(-butyl),2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba,diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat,diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor,dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid,diquat, dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb,ethalfluralin, ethametsulfuron(-methyl), ethofumesate, ethoxyfen,ethoxysulfuron, etobenzanid, fenoxaprop-(-P-ethyl), fentrazamide,flamprop(-isopropyl), flamprop lamprop(-methyl), flazasulfuron,florasulam, fluazifop(-P-butyl), fluazolate, flucarbazone, flufenacet,flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn,flumetsulam, fluometuron, fluorochloridone, fluoroglycofen(-ethyl),flupoxam, flupropacil, flurpyrsulfuron(-methyl, -sodium),flurenol(-butyl), fluridone, fluroxypyr(-meptyl), flurprimidol,flurtamone, fluthiacet(-methyl), fluthiamide, fomesafen,glufosinate(-ammonium), glyphosate(-isopropylammonium), halosafen,haloxyfop(-ethoxyethyl), haloxyfop(-P-methyl), hexazinone,imazamethabenz(-methyl), imazamethapyr, imazamox, imazapic, imazapyr,imazaquin, imazethapyr, imazosulfuron, iodosulfuron(-methyl, -sodium),ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP,mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron,metobenzuron, metobromuron, (alpha-)metolachlor, metosulam, metoxuron,metribuzin, metsulfuron(-methyl), molinate, monolinuron, naproanilide,napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin,oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen,paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone,phenmedipham, piperophos, pretilachlor, primisulfuron(-methyl),prometryn, propachlor, propanil, propaquizafop, propisochlor,propyzamide, prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazolate,pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb,pyridate, pyriminobac(-methyl), pyrithiobac(-sodium), quinchlorac,quinmerac, quinoclamine, quizalofop(-P-ethyl), quizalofop(-P-tefuryl),rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone,sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr,thidiazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil,tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr,tridiphane, trifluralin and triflusulfuron.

A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing, scattering.

The active compounds according to the invention can be applied bothbefore and after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a relatively widerange. It depends essentially on the nature of the desired effect. Ingeneral, the amounts used are between 1 g and 10 kg of active compoundper hectare of soil surface, preferably between 5 g and 5 kg per ha.

The preparation and the use of the active compounds according to theinvention can be seen from the examples below.

PREPARATION EXAMPLES EXAMPLE 1

(Process (a))

0.76 g (2.9 mmol) of5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-oneare dissolved in 40 ml of acetonitrile and, at room temperature (about20° C.) admixed a little at a time and with stirring with 0.75 g (3.2mmol) of 4-methoxycarbonyl-2-methyl-thiophene-3-sulphonamide and 0.49 g(3.2 mmol) of 1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU). The reactionmixture is stirred at room temperature for 12 hours and thenconcentrated under reduced pressure. The residue is taken up inmethylene chloride, washed successively with 1 N hydrochloric acid andwater, dried with sodium sulphate and filtered. The filtrate isconcentrated under water pump vacuum, the residue is digested withisopropanol and the resulting crystalline product is isolated byfiltration with suction.

This gives 0.70 g (60% of theory) of methyl4-[[[(3-ethoxy-4,5-dihydro-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-carbonyl]-amino]-sulphonyl]-5-methyl-thiophene-3-carboxylate(alias5-ethoxy-4-methyl-2-[(4-methoxycarbonyl-2-methyl-thien-3-yl)-sulphonyl-amino-carbonyl]-2,4-dihydro-3H-1,2,4-triazol-3-one)of melting point 163° C.

Analogously to Example 1, and in accordance with the general descriptionof the preparation processes according to the invention, it is alsopossible to prepare, for example, the compounds of the general formula(I) listed in Table 1 below. TABLE 1 Examples of compounds of theformula (I) (I)

Ex. Melting No. Q¹ Q² R¹ R² R³ R⁴ point (° C.) 2 O O CH₃ CH₃ OCH₃ CH₃201 3 O O CH₃ CH₃ OC₃H7-n CH₃ 156 4 O O CH₃ CH₃ OC₃H7-i CH₃ 150 5 O OCH₃ CH₃ OCH₃

218 6 O O CH₃ CH₃ OC₂H₅

170 7 O O CH₃ CH₃ OC₃H₇-n

156 8 O O CH₃ CH₃ OC₃H₇-i

188 9 O O CH₃ CH₃

200 10 O O CH₃ CH₃ CH₃ CH₃ 178 11 O O CH₃ CH₃ C₂H₅ CH₃ 161 12 O O CH₃CH₃ SCH₃ CH₃ 183Starting Materials of the Formula (II):

EXAMPLE (II-1)

A mixture of 45 g (177 mmol) of4-methoxycarbonyl-2-methyl-thiophene-3-sulphonyl chloride, 34 g (354mmol) of ammonium carbonate and 400 ml of methylene chloride is stirredat room temperature (about 20° C.) for 12 hours. The mixture is filteredand the solvent is then distilled off from the filtrate under water pumpvacuum, the residue is digested with diethyl ether and the crystallineproduct is isolated by filtration with suction. This gives 21.5 g (52%of theory) of 4-methoxy-carbonyl-2-methyl-thiophene-3-sulphonamide.

Analogously to Example (II-1), it is also possible to prepare, forexample, the following compounds of the general formula (II):

-   -   4-ethoxycarbonyl-2-methyl-thiophene-3-sulphonamide,    -   4-n-propoxycarbonyl-2-methyl-thiophene-3-sulphonamide,    -   4-i-propoxycarbonyl-2-methyl-thiophene-3-sulphonamide,    -   4-methoxycarbonyl-2-ethyl-thiophene-3-sulphonamide,    -   4-ethoxycarbonyl-2-ethyl-thiophene-3-sulphonamide,    -   4-n-propoxycarbonyl-2-ethyl-thiophene-3-sulphonamide,    -   4-i-propoxycarbonyl-2-ethyl-thiophene-3-sulphonamide,    -   4-methoxycarbonyl-2-n-propyl-thiophene-3-sulphonamide,    -   4-ethoxycarbonyl-2-n-propyl-thiophene-3-sulphonamide,    -   4-n-propoxycarbonyl-2-n-propyl-thiophene-3-sulphonamide,    -   4-i-propoxycarbonyl-2-n-propyl-thiophene-3-sulphonamide,    -   4-methoxycarbonyl-2-i-propyl-thiophene-3-sulphonamide,    -   4-ethoxycarbonyl-2-i-propyl-thiophene-3-sulphonamide,    -   4-n-propoxycarbonyl-2-i-propyl-thiophene-3-sulphonamide,    -   4-i-propoxycarbonyl-2-i-propyl-thiophene-3-sulphonamide.        Starting Materials of the Formula (VI):

EXAMPLE (VI-1)

At from 0° C. to 5° C., a solution of 19.9 g (0.29 mol) of sodiumnitrite in 60 ml of water is added dropwise with stirring to a solutionof 42.7 g (0.25 mol) of methyl 3-amino-2-methyl-thiophene-4-carboxylatein 75 ml of 10% strength aqueous hydrochloric acid. The reaction mixtureis stirred at from 0° C. to 5° C. for 60 minutes. The excess of nitrideis then destroyed using amidosulphonic acid. At from 0° C. to 5° C., themixture is then added dropwise with stirring to a solution of 35 g (0.55mol) of sulphur dioxide in 300 ml of methylene chloride. After additionof 1.5 g of copper(I) chloride and 1.5 g of dodecyl-trimethylammoniumbromide, the reaction mixture is stirred at 40° C. for 60 minutes andthen at 20° C. for 12 hours. 18 ml of 35% strength aqueous hydrochloricacid are then added, the mixture is stirred at 20° C. for 4 hours andthe phases are then separated. The aqueous phase is re-extracted withmethylene chloride and the combined organic phases are washed withwater, dried with magnesium sulphate and filtered. The filtrate isconcentrated under water pump vacuum and the residue is crystallizedfrom hexane.

This gives 51.7 g (81% of theory) of4-methoxycarbonyl-2-methyl-thiophene-3-sulphonyl chloride.

Analogously to Example (VI-1), it is also possible to prepare, forexample, the following compounds of the formula (VI):

-   -   4-ethoxycarbonyl-2-methyl-thiophene-3-sulphonyl chloride,    -   4-n-propoxycarbonyl-2-methyl-thiophene-3-sulphonyl chloride,    -   4-i-propoxycarbonyl-2-methyl-thiophene-3-sulphonyl chloride,    -   4-methoxycarbonyl-2-ethyl-thiophene-3-sulphonyl chloride,    -   4-ethoxycarbonyl-2-ethyl-thiophene-3-sulphonyl chloride,    -   4-n-propoxycarbonyl-2-ethyl-thiophene-3-sulphonyl chloride,    -   4-i-propoxycarbonyl-2-ethyl-thiophene-3-sulphonyl chloride,    -   4-methoxycarbonyl-2-n-propyl-thiophene-3-sulphonyl chloride,    -   4-ethoxycarbonyl-2-n-propyl-thiophene-3-sulphonyl chloride,    -   4-n-propoxycarbonyl-2-n-propyl-thiophene-3-sulphonyl chloride,    -   4-i-propoxycarbonyl-2-n-propyl-thiophene-3-sulphonyl chloride,    -   4-methoxycarbonyl-2-i-propyl-thiophene-3-sulphonyl chloride,    -   4-ethoxycarbonyl-2-i-propyl-thiophene-3-sulphonyl chloride,    -   4-n-propoxycarbonyl-2-i-propyl-thiophene-3-sulphonyl chloride,    -   4-i-propoxycarbonyl-2-i-propyl-thiophene-3-sulphonyl chloride.        Starting Materials of the Formula (X):

EXAMPLE (X-1)

Under water pump vacuum, 61 g of a 20% strength solution of sodiumethoxide in ethanol (213 mmol of NaOCH₃) are evaporated to dryness. Theresidue is taken up in 80 ml of toluene, and 28.6 g (109 mmol) of ethyl2-(2-ethoxycarbonyl-ethylthio)-3-methyl-butyrate are then added and thereaction mixture is stirred at from 70° C. to 80° C. for 12 hours. Aftercooling to room temperature, the mixture is poured into ice-water andthen acidified with conc. hydrochloric acid. The organic phase is thenseparated off, the aqueous phase is re-extracted with diethyl ether andthe organic phases are combined, dried with magnesium sulphate andfiltered. The filtrate is concentrated under water pump vacuum and theresidue is purified by distillation under reduced pressure.

This gives 22.6 g (96% of theory) of ethyl5-i-propyl-4-oxo-tetrahydrothiophene-3-carboxylate of boiling point 115°C. (at 0.5 mbar).

A mixture of 38 g (176 mmol) of ethyl5-i-propyl-4-oxo-tetrahydrothiophene-3-carboxylate, 35 g ofhydroxylamine hydrochloride, 53 g of barium carbonate and 300 ml ofethanol is heated under reflux for 12 hours and then filtered whilststill hot. The filtrate is concentrated under water pump vacuum, and theresidue is taken up in diethyl ether, washed with water, dried withmagnesium sulphate and filtered. From the filtrate, the solvent iscarefully distilled off under reduced pressure.

This give 34.2 g (86% of theory) of ethyl4-hydroximino-5-i-propyl-dihyro-5H-thiophene-3-carboxylate as an oilwhich can be reacted further without any further purification.

33 g (143 mmol) of ethyl4-hydroximino-5-i-propyl-dihydro-5H-thiophene-3-carboxylate aredissolved in 250 ml of diethyl ether and, with ice-cooling, hydrogenchloride is introduced for 20 minutes (until saturation has beenreached). The mixture is allowed to stand at room temperature (about 20°C.) for 2 days and then concentrated under water pump vacuum, and theresidue is crystallized from acetone.

This gives 13 g (37% of theory) of ethyl4-amino-5-i-propyl-thiophene-3-carboxylate hydrochloride as a solidproduct.

EXAMPLE (X-2)

A mixture of 310 g (1.78 mol) of methyl5-methyl-4-oxo-tetrahydrothiophene-3-carboxylate, 155 g (2.27 mol) ofhydroxylamine hydrochloride and 900 ml of acetonitrile is heated underreflux for 60 minutes. After cooling to room temperature (about 20° C.),the resulting crystalline product is isolated by filtration withsuction.

This gives 335 g (91% of theory) of methyl4-amino-5-methyl-thiophene-3-carboxylate hydrochloride of melting point132° C.

273 g (1.62 mol) of methyl 4-amino-5-methyl-thiophene-3-carboxylatehydrochloride are dissolved in 1 litre of water, and 2 litres ofmethylene chloride are added below the layer of water. With vigorousstirring, 125 g of sodium bicarbonate are then added, and the mixture isstirred for another 15 minutes. The organic phase is separated off,dried with magnesium sulphate and filtered. The filtrate is concentratedunder water pump vacuum, the residue is digested with petroleum etherand the crystalline product is isolated by filtration with suction.

This gives 148 g (53% of theory) of methyl4-amino-5-methyl-thiophene-3-carboxylate of melting point 78° C.

Analogously to Examples (X-1) and (X-2), it is also possible to prepare,for example, the following compounds of the general formula (X):

-   -   ethyl 4-amino-5-methyl-thiophene-3-carboxylate    -   (m.p.: 50° C., hydrochloride: m.p.: 143° C.),    -   n-propyl 4-amino-5-methyl-thiophene-3-carboxylate,    -   i-propyl 4-amino-5-methyl-thiophene-3-carboxylate,    -   methyl 4-amino-5-ethyl-thiophene-3-carboxylate,    -   ethyl 4-amino-5-ethyl-thiophene-3-carboxylate,    -   n-propyl 4-amino-5-ethyl-thiophene-3-carboxylate,    -   (oil, hydrochloride: m.p.: 140° C.),    -   i-propyl 4-amino-5-ethyl-thiophene-3-carboxylate,    -   (oil, hydrochloride: m.p.: 142° C.),    -   methyl 4-amino-5-n-propyl-thiophene-3-carboxylate,    -   ethyl 4-amino-5-n-propyl-thiophene-3-carboxylate,    -   n-propyl 4-amino-5-n-propyl-thiophene-3-carboxylate,    -   i-propyl 4-amino-5-n-propyl-thiophene-3-carboxylate,    -   methyl 4-amino-5-i-propyl-thiophene-3-carboxylate,    -   n-propyl 4-amino-5-i-propyl-thiophene-3-carboxylate,    -   i-propyl 4-amino-5-i-propyl-thiophene-3-carboxylate,    -   and in each case the corresponding hydrochlorides.

USE EXAMPLES EXAMPLE A

Pre-Emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours,the soil is sprayed with the preparation of active compound such thatthe particular amount of active compound desired is applied per unitarea. The concentration of the spray liquor is chosen so that theparticular amount of active compound desired is applied in 1000 litresof water per hectare.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control.

The figure denote:

-   -   0%=no effect (like untreated control)    -   100%=total destruction

In this test, for example, the compounds of Preparation Examples 1, 2,3, 4, 5, 6, 7, 8, 9, 10, 11 and 12 exhibit very strong activity againstweeds, and some of them are tolerated well by crop plants, such as, forexample, cotton, maize and wheat. TABLE A1 Pre-emergence test/greenhouseActive compound of Application rate Preparation Example No. (g of ai/ha)Alopecurus Cyperus Setaria Abutilon Amaranthus Galium Sinapis Xanthium(2) 60 95 100 95 95 100 — 95 100 (5) 250 99 100 100 95 100 95 95 99 (6)250 95 100 100 100 95 90 95 95 (7) 250 90 100 95 95 95 95 95 — (9) 25095 100 100 100 100 95 95 — (10) 250 95 95 100 95 100 95 100 90

TABLE A2 Pre-emergence test/greenhouse Active compound of Applicationrate Preparation Example No. (g of ai/ha) Alopecurus Bromus SetariaChenopodium Matricaria Stellaria Veronica Viola (1) 60 90 90 90 100 9595 100 100

TABLE A3 Pre-emergence test/greenhouse Active compound of Applicationrate Preparation Example No. (g of ai/ha) Wheat Barley AlopecurusAmaranthus Solanum Stellaria (3) 60 0 0 80 95 90 95

TABLE A4 Pre-emergence test/greenhouse Active compound of Applicationrate Preparation Example No. (g of ai/ha) Wheat Bromus CyperusEchinochloa Solanum Stellaria Veronica Viola (4) 125 20 100 100 100 100100 100 100

TABLE A5 Pre-emergence test/greenhouse Active compound of Applicationrate Preparation Example No. (g of ai/ha) Cotton Bromus EchinochloaChenopodium Solanum Stellaria Veronica Viola (8) 60 0 90 90 90 90 95 95100

TABLE A6 Pre-emergence test/greenhouse Active compound of PreparationApplication rate Example No. (g of ai/ha) Maize Alopecurus DigitariaSetaria Amaranthus Chenopodium Matricaria Solanum (11) 60 10 100 100 100100 100 100 100

TABLE A7 Pre-emergence test/greenhouse Active compound of Applicationrate Preparation Example No. (g of ai/ha) Maize Bromus Cyperus SetariaAbutilon Stellaria Veronica Viola (12) 60 10 100 100 100 100 100 100 100

EXAMPLE B

Post-Emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, one part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with thepreparation of active compound such that the particular amounts ofactive compound desired are applied per unit area. The concentration ofthe spray liquor is chosen so that the particular amounts of activecompound desired are applied in 1000 l of water/ha.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control.

The figures denote:

-   -   0%=no effect (like untreated control)    -   100%=total destruction

In this test, for example, the compounds of Preparation Examples 1, 2,3, 4, 5, 6, 7, 8, 9, 10, 11 and 12 exhibit very strong activity againstweeds, and some of them are tolerated well by crop plants, such as, forexample, barley and wheat. TABLE B1 Post-emergence test/greenhouseActive compound of Preparation Application rate Example No. (g of ai/ha)Wheat Alopecurus Echinochloa Abutilon Amaranthus Matricaria SolanumStellaria (3) 15 0 70 60 95 95 90 95 100

TABLE B2 Post-emergence test/greenhouse Active compound of Applicationrate Preparation Example No. (g of ai/ha) Wheat Abutilon AmaranthusIpomoea Matricaria Solanum Stellaria (4) 8 10 95 95 95 90 95 95

TABLE B3 Post-emergence test/greenhouse Active compound of PreparationApplication rate Example No. (g of ai/ha) Barley Wheat EchinochloaAmaranthus Chenopodium Stellaria Veronica Viola (5) 2 10 10 95 99 95 10090 90

TABLE B4 Post-emergence test/greenhouse Active compound of Applicationrate Preparation Example No. (g of ai/ha) Wheat Maize Setaria AbutilonAmaranthus Solanum Stellaria (10) 15 10 10 95 90 90 90 95

TABLE B5 Post-emergence test/greenhouse Active compound of Applicationrate Preparation Example No. (g of ai/ha) Alopecurus Avenafatua SetariaAbutilon Amaranthus Sinapis Xanthium (2) 60 95 80 100 100 100 100 100(1) 250 100 100 100 100 100 100 100 (6) 250 100 100 100 100 100 100 100(7) 250 95 100 90 100 100 100 90 (8) 250 100 100 100 100 100 95 100 (9)250 100 100 100 100 100 100 100 (11) 250 100 100 100 100 100 100 100(12) 250 95 100 100 100 100 100 100

1-10. (canceled)
 11. A compound of the formula (I)

wherein Q¹ represents O or S, Q² represents O or S, R¹ represents ineach case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl,cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, R²represents hydrogen, cyano, nitro, halogen or represents in each caseoptionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio,alkylsulphinyl, alkylsulphonyl, alkenyl, alkinyl, alkenyloxy oralkinyloxy, R³ represents hydrogen, hydroxyl, mercapto, amino, cyano,halogen or represents in each case optionally substituted alkyl,alkenyl, alkinyl, alkoxy, alkylthio, alkylamino, alkylcarbonylamino,alkenyloxy, alkinyloxy, alkenylthio, alkinylthio, alkenylamino,alkinylamino, dialkylamino, aziridino, pyrrolidino, piperidino,morpholino, cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkylthio,cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio,cycloalkylalkylamino, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio,arylalkylthio, arylamino or arylalkylamino, and R⁴ represents hydrogen,hydroxyl, amino, cyano, represents alkylideneamino or represents in eachcase optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkylamino,alkyl-carbonylamino, alkenyloxy, dialkylamino, cycloalkyl,cycloalkylamino, cycloalkylalkyl, aryl or arylalkyl, or R³ and R⁴together represent optionally branched alkanediyl, or one or more saltsof the compound of the formula (I), excluding the compound where Q¹ andQ² each represents O, R¹, R², and R⁴ each represents —CH₃, and R³represents —OCH₃.
 12. The compound according to claim 11, wherein Q¹represents O or S, Q² represents O or S, R¹ represents optionallycyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl having 1 to 6 carbonatoms, represents in each case optionally cyano- or halogen-substitutedalkenyl or alkinyl having in each case 2 to 6 carbon atoms, representsin each case optionally cyano-, halogen- or C₁-C₄-alkyl-substitutedcycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms inthe cycloalkyl group and optionally 1 to 4 carbon atoms in the alkylmoiety, represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted aryl or arylalkyl having ineach case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4carbon atoms in the alkyl moiety, or represents in each case optionallynitro-, cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substitutedheterocyclyl or heterocyclylalkyl having in each case up to 6 carbonatoms and additionally 1 to 4 nitrogen atoms and/or 1 to 2 oxygen orsulphur atoms in the heterocyclyl group and optionally 1 to 4 carbonatoms in the alkyl moiety, R² represents hydrogen, cyano, nitro,halogen, represents in each case optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio,alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atomsin the alkyl group, or represents in each case optionally cyano- orhalogen-substituted alkenyl, alkinyl, alkenyloxy or alkinyloxy having ineach case 2 to 6 carbon atoms in the alkenyl or alkinyl group, R³represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine,chlorine, bromine, iodine, represents optionally fluorine-, chlorine-,bromine-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- orC₁-C₄-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms,represents in each case optionally fluorine-, chlorine- and/orbromine-substituted alkenyl or alkinyl having in each case 2 to 6 carbonatoms, represents in each case optionally fluorine-, chlorine-, cyano-,C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substituted alkoxy, alkylthio,alkylamino or alkylcarbonylamino having in each case 1 to 6 carbon atomsin the alkyl group, represents alkenyloxy, alkinyloxy, alkenylthio,alkinylthio, alkenylamino or alkinylamino having in each case 3 to 6carbon atoms in the alkenyl or alkinyl group, represents dialkylaminohaving in each case 1 to 4 carbon atoms in the alkyl groups, representsin each case optionally methyl- and/or ethyl-substituted aziridino,pyrrolidino, piperidino or morpholino, represents in each caseoptionally fluorine-, chlorine-, bromine-, cyano- and/orC₁-C₄-alkyl-substituted cycloalkyl, cycloalkenyl, cycloalkyloxy,cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy,cycloalkylalkylthio or cycloalkylalkylamino having in each case 3 to 6carbon atoms in the cycloalkyl or cycloalkenyl group and optionally 1 to4 carbon atoms in the alkyl moiety, or represents in each caseoptionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C₁-C₄-alkyl-,trifluoromethyl-, C₁-C₄-alkoxy- and/or C₁-C₄-alkoxy-carbonyl-substitutedaryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylaminoor arylalkylamino having in each case 6 or 10 carbon atoms in the arylgroup and optionally 1 to 4 carbon atoms in the alkyl moiety, and R⁴represents hydrogen, hydroxyl, amino, cyano, representsC₂-C₁₀-alkylideneamino, represents optionally fluorine-, chlorine-,bromine-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- orC₁-C₄-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms,represents in each case optionally fluorine-, chlorine- and/orbromine-substituted alkenyl or alkinyl having in each case 2 to 6 carbonatoms, represents in each case optionally fluorine-, chlorine-,bromine-, cyano-, C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substitutedalkoxy, alkylamino or alkylcarbonylamino having in each case 1 to 6carbon atoms in the alkyl group, represents alkenyloxy having 3 to 6carbon atoms, represents dialkylamino having in each case 1 to 4 carbonatoms in the alkyl groups, represents in each case optionally fluorine-,chlorine-, bromine-, cyano- and/or C₁-C₄-alkyl-substituted cycloalkyl,cycloalkylamino or cycloalkylalkyl having in each case 3 to 6 carbonatoms in the alkyl group and optionally 1 to 4 carbon atoms in the alkylmoiety, or represents in each case optionally fluorine-, chlorine-,bromine-, cyano-, nitro-, C₁-C₄-alkyl-, trifluoromethyl- and/orC₁-C₄-alkoxy-substituted aryl or arylalkyl having in each case 6 or 10carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in thealkyl moiety, or R³ and R⁴ together represent optionally branchedalkanediyl having 3 to 6 carbon atoms, and a sodium, potassium,magnesium, calcium, ammonium, C₁-C₄-alkyl-ammonium,di-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-ammonium,tetra-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-sulphonium, C₅- orC₆-cycloalkyl-ammonium and di-(C₁-C₂-alkyl)-benzylammonium salt of saidcompound of the formula (I).
 13. The compound according to claim 11wherein Q¹ represents O or S, Q² represents O or S, R¹ represents ineach case optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,represents in each case optionally cyano-, fluorine- orchlorine-substituted propenyl, butenyl, propinyl or butinyl, representsin each case optionally cyano-, fluorine-, chlorine-, methyl- orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, represents in each case optionally cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-,methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenyl, phenylmethyl or phenylethyl, orrepresents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methyl-, ethyl-, n- or i-propyl-, methoxy-, ethoxy-, n- ori-propoxy-substituted heterocyclyl or heterocyclylmethyl, where theheterocyclyl group is in each case selected from the group consisting ofoxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl,R² represents hydrogen, cyano, fluorine, chlorine, bromine, representsin each case optionally cyano-, fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- ori-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, orrepresents in each case optionally cyano-, fluorine- orchlorine-substituted propenyl, butenyl, propinyl, butinyl, propenyloxy,butenyloxy, propinyloxy or butinyloxy, R³ represents hydrogen, hydroxyl,mercapto, amino, cyano, fluorine, chlorine, bromine, represents in eachcase optionally fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- ori-propoxy, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-,ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, represents in each case optionallyfluorine-, chlorine- and/or bromine-substituted ethenyl, propenyl,butenyl, ethinyl, propinyl or butinyl, represents in each caseoptionally fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- ori-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-,s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- ort-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- ort-butylamino, acetylamino or propionylamino, represents propenyloxy,butenyloxy, ethinyloxy, propinyloxy, butinyloxy, propenylthio,butenylthio, propinylthio, butinylthio, propenylamino, butenylamino,propinylamino or butinylamino, represents dimethylamino, diethylamino ordipropylamino, represents in each case optionally fluorine-, chlorine-,methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy,cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio,cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino,cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy,cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy,cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio,cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino,cyclopentylmethylamino or cyclohexylmethylamino, or represents in eachcase optionally fluorine-, chlorine-, bromine-, methyl-,trifluoromethyl-, methoxy- or methoxy-carbonyl-substituted phenyl,benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino orbenzylamino, and R⁴ represents hydrogen, hydroxyl, amino, represents ineach case optionally fluorine-, chlorine-, cyano-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,represents in each case optionally fluorine-, chlorine- and/orbromine-substituted ethenyl, propenyl, butenyl, propinyl or butinyl,represents in each case optionally fluorine-, chlorine-, cyano-,methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-,s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s-or t-butylamino, represents propenyloxy or butenyloxy, representsdimethylamino or diethylamino, represents in each case optionallyfluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino,cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl or cyclohexylmethyl, or represents in each caseoptionally fluorine-, chlorine-, methyl-, trifluoromethyl- and/ormethoxy-substituted phenyl or benzyl, or R³ and R⁴ together representtrimethylene (propane-1,3-diyl), tetramethylene (butane-1,4-diyl) orpentamethylene (pentane-1,5-diyl), and a sodium, potassium, magnesium,calcium, ammonium, C₁-C₄-alkyl-ammonium, di-(C₁-C₄-alkyl)-ammonium,tri-(C₁-C₄-alkyl)-ammonium, tetra-(C₁-C₄-alkyl)-ammonium,tri-(C₁-C₄-alkyl)-sulphonium, C₅- or C₆-cycloalkyl-ammonium anddi-(C₁-C₂-alkyl)-benzylammonium salt of said compound.
 14. A compoundaccording to claim 11 wherein Q¹ represents O, Q² represents O, R¹represents in each case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, R² representsfluorine, chlorine, bromine or represents in each case optionallyfluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n-or i-propyl, R³ represents hydrogen, chlorine, bromine, represents ineach case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-substituted methyl, ethyl, n- or i-propyl, represents in eachcase optionally fluorine- or chlorine-substituted ethenyl, propenyl,butenyl, propinyl or butinyl, represents in each case optionallyfluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substitutedmethoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- ori-propylthio, methylamino, ethylamino, n- or i-propylamino, representspropenyloxy, propinyloxy, propenylthio, propinylthio, propenylamino orpropinylamino, represents dimethylamino or diethylamino, represents ineach case optionally fluorine-, chlorine- or methyl-substitutedcyclopropyl, cyclopropyloxy, cyclopropylmethyl or cyclopropylmethoxy,and R⁴ represents in each case optionally fluorine-, chlorine-, methoxy-or ethoxy-substituted methyl, ethyl, n- or i-propyl, represents in eachcase optionally fluorine- or chlorine-substituted ethenyl, propenyl orpropinyl, represents in each case optionally fluorine-, chlorine-,methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy,represents methylamino, or represents cyclopropyl, and a sodium,potassium, magnesium, calcium, ammonium, C₁-C₄-alkyl-ammonium,di-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-ammonium,tetra-(C₁-C₄-alkyl)-ammonium, tri-(C₁-C₄-alkyl)-sulphonium, C₅- orC₆-cycloalkyl-ammonium and di-(C₁-C₂-alkyl)-benzylammonium salt of saidcompound.
 15. A process for preparing a compound according to claim 11,said process being selected from the group consisting of process (a),process (b), process (c), process (d) and process (e), wherein (a) saidprocess (a) comprises the step of reacting a substitutedthiophene-3-sulphonamide of the formula (II)

wherein R¹ and R² are each as defined in claim 11 with a substitutedtriazolin(ethi)one of the formula (III)

wherein Q¹, Q², R³ and R⁴ are each as defined in claim 11 and Zrepresents halogen, alkoxy, aryloxy or arylalkoxy, optionally in thepresence of a reaction auxiliary and optionally in the presence of adiluent, (b) said process (b) comprises the step of reacting asubstituted thien-3-yl-sulphonyl iso(thio)cyanate of the formula (IV)

wherein Q¹, R¹ and R² are each as defined in claim 11, with atriazolin(ethi)one of the formula (V)

wherein Q², R⁴ and R⁵ are each as defined in claim 11, optionally in thepresence of a reaction auxiliary and optionally in the presence of adiluent, (c) said process (c) comprises the step of reacting asubstituted thiophene-3-sulphonyl chloride of the formula (VI)

wherein R¹ and R² are each as defined in claim 11, with atriazolin(ethi)one of the formula (V)

wherein Q², R⁴ and R⁵ are each as defined in claim 11 and a metal(thio)cyanate of the formula (VII)M-Q¹-CN   (VII) wherein Q¹ is as defined in claim 11, optionally in thepresence of a reaction auxiliary and optionally in the presence of adiluent, (d) said process (d) comprises the step of reacting asubstituted thiophene-3-sulphonyl chloride of the formula (VI)

wherein R¹ and R² are each as defined in claim 11 with atriazolin(ethi)one-(thio)carboxamide of the formula (VIII)

wherein Q¹, Q², R³ and R⁴ are each as defined in claim 11, optionally inthe presence of a reaction auxiliary and optionally in the presence of adiluent, and (e) said process (e) comprises the step of reacting asubstituted thien-3-yl-sulphonylamino(thio)carbonyl compound of theformula (IX)

wherein Q¹, R¹ and R² are each as defined in claim 11 and Z representshalogen, alkoxy, aryloxy or arylalkoxy, with a triazolin(ethi)one of theformula (V)

wherein Q², R⁴ and R⁵ are each as defined in claim 11, optionally in thepresence of a reaction auxiliary and optionally in the presence of adiluent, wherein each of said processes (a), (b), (c), (d) and (e)further optionally comprises the step of converting the compound of theformula (I) obtained by said processes (a), (b), (c), (d) and (e), intoa salt.
 16. A compound of the formula (II)

wherein R¹ and R² are each as defined in claim 11, excluding thecompound 4-methoxycarbonyl-thiophene-3-sulphonamide.
 17. A compound ofthe formula (VI)

wherein R¹ and R² are each as defined in claim 11, excluding thecompound 4-methoxycarbonyl-thiophene-3-sulphonyl chloride.
 18. A methodfor controlling undesirable vegetation, comprising the step of allowingone or more compounds according to claim 11 to act on a member selectedfrom the group consisting of an undesirable plant, a habitat of saidundesirable plant and combinations thereof.
 19. An herbicidalcomposition comprising one or more compounds according to claim 11 and amember selected from the group consisting of one or more extenders, oneor more surfactants, and combinations thereof.